Chicago.com no longer a directory; owner also powering new email service at Power.com.

This morning I read an article by Robin Wauters lampooning Power.com, which offers an @Power.com email address and subdomains for a very steep price.

The site immediately reminded me of Chicago.com and its personalized @chicago.com email addresses. Indeed, Power.com is “powered” by @Identity, a company formed by Chicago.com owner Josh Metnick and Thought Convergence’s Ammar Kubba.

As I looked into this story I went to Chicago.com and was surprised to be forwarded to identity.chicago.com — a page pitching @Chicago.com email addresses.

The Chicago directory is gone. Or at least hidden. Metnick is going all in with email addresses.

He’s had some success selling these addresses, and I guess it makes more money than the Chicago.com directory. (I’ve reached out to Metnick for comment.)

But I think selling @Chicago.com addresses is very different from @Power.com. I certainly wouldn’t expect an @power email address to sell for more than @chicago.

When Robin checked Robin@power.com, he was quoted $7,576 for a five year term. Robin@chicago.com is (a still steep) $749 per year.

As you can tell from the comments to Robin’s story, it’s not easy to convince people they should pay for a vanity email address. There are plenty of vanity email address for free or at a very low cost.

I reached out to the whois contact on Power.com, Leigh Power. His company Power Assist, Inc. has owned the domain since 1992.

He said the pricing is by design.

“This is obviously designed to be for a rather exclusive group of people,” he said. “I don’t think the person that goes for a free email at Gmail will go out for it. We hope there’s a small group of folks who will be interested.”

The venture is being run by Scott Smith, a Canadian entrepreneur (and DNForum member). Smith tried to broker the Power.com domain last year to no avail. I’m chatting with him later today and will update this story.

With regards to vanity email services in general, I imagine customers will be concerned with who actually owns their email address. If you’re a business customer using an @Chicago.com address, what happens if Chicago.com suddenly shuts down?

Selfishly, I’d love to see this form of domain monetization take off. But you can call me a skeptic (at least at these prices). I’m glad other people are trying it instead of me.

Chicago.com, Inc., has filed a trademark application with the U.S. Patent and Trademark office for the DotChicago mark. But Chicago.com founder Josh Metnick says his company did not apply for the top level domain .Chicago with ICANN.

The application, filed May 31, states that the mark is for “Domain name registration services; Domain name registration services, namely, conducting domain name searches for the purpose of providing legal advice on domain name registration”.

The application claims that Chicago.com, Inc. has been using the mark in commerce since “as early as 05/01/2012″. As proof, the application includes a copy of this page from Chicago.com’s web site.

This isn’t actually for second level domains; it’s for third level domains such as realestate.chicago.com. The examples listed on the page resolve to Google Sites pages.

The page also states “Since 2005, Chicago.com, Inc. has been providing a “.Chicago” directory of Chicago metropolitan area goods and services.”

Metnick told me Chicago.com has been offering these domains since 2005.

The wording on the page may seem peculiar for a third level domain. But Metnick claims “for domainers it’s probably confusing, but for most business owners it’s not.” The message on the @chicago Twitter page is more clear: “Get yourname@chicago.com or register your idea.chicago.com”

Chicago.com has had quite a bit of success parceling off identities under the .chicago web address, including selling e-mail addresses. Some people who have bought email addresses have also picked up the corresponding rights to the third level domain.

Chicago.com has two granted U.S. trademarks including THE .CHICAGO LOWDOWN for its newsletter. It tried and failed to register .chicago with the U.S. Patent and Trademark Office in 2005.

It also has a number of State of Illinois trademarks, including .chicago. It has filed trademarks for some of its third level domains, too, but in a way that makes them look like second level domains. One example: realestate.chicago.

This could make for an interesting scenario if .chicago ever exists as a top level domain.

“We want to own the top level domain,” Metnick admits. “That’s our goal. We’ve been using the name since 2005 and we don’t know anyone else who’s using it…They’re our marks. We were the first ones using them.”

Metnick says his company might apply for .chicago (the top level domain) in the future if it has the resources.